One-pot functionalisation of N-substituted tetrahydroisoquinolines by photooxidation and tunable organometallic trapping of iminium intermediates

Joshua Barham, Matthew P John, John A Murphy

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13 Citations (Scopus)
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Abstract

Nucleophilic trapping of iminium salts generated via oxidative functionalisation of tertiary amines is well established with stabilised carbon nucleophiles. The few reports of organometallic additions have limited scope of substrate and organometallic nucleophile. We report a novel, one-pot methodology that functionalises N-substituted tetrahydroisoquinolines by visible lightassisted photooxidation, followed by trapping of the resultant iminium ions with organometallic nucleophiles. This affords 1,2-disubstituted tetrahydroisoquinolines in moderate to excellent yields.
Original languageEnglish
Pages (from-to)2981-2988
Number of pages8
JournalBeilstein Journal of Organic Chemistry
Volume10
DOIs
Publication statusPublished - 12 Dec 2014

Fingerprint

Tetrahydroisoquinolines
Nucleophiles
Photooxidation
Organometallics
Amines
Carbon
Salts
Ions
Substrates

Keywords

  • iminium salt
  • organometallic
  • oxidative functionalisation
  • photoredox catalysis
  • tetrahydroisoquinoline

Cite this

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AU - Murphy, John A

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AB - Nucleophilic trapping of iminium salts generated via oxidative functionalisation of tertiary amines is well established with stabilised carbon nucleophiles. The few reports of organometallic additions have limited scope of substrate and organometallic nucleophile. We report a novel, one-pot methodology that functionalises N-substituted tetrahydroisoquinolines by visible lightassisted photooxidation, followed by trapping of the resultant iminium ions with organometallic nucleophiles. This affords 1,2-disubstituted tetrahydroisoquinolines in moderate to excellent yields.

KW - iminium salt

KW - organometallic

KW - oxidative functionalisation

KW - photoredox catalysis

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